AR067977A1 - DERIVATIVES OF PIRIDINE AND ITS USE AS IMMUNOMODULATORS - Google Patents

DERIVATIVES OF PIRIDINE AND ITS USE AS IMMUNOMODULATORS

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Publication number
AR067977A1
AR067977A1 ARP080103611A ARP080103611A AR067977A1 AR 067977 A1 AR067977 A1 AR 067977A1 AR P080103611 A ARP080103611 A AR P080103611A AR P080103611 A ARP080103611 A AR P080103611A AR 067977 A1 AR067977 A1 AR 067977A1
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Argentina
Prior art keywords
alkyl
hydrogen
compound
methoxy
attached
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ARP080103611A
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Spanish (es)
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Actelion Pharmaceuticals Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Endocrinology (AREA)
  • Dermatology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Oncology (AREA)
  • Obesity (AREA)
  • Psychiatry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Emergency Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Transplantation (AREA)
  • Otolaryngology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Dichos compuestos actuan particularmente como agentes inmunomoduladores. Reivindicacion 1: Un compuesto de formula (1), Piridina1-A-Piridiria2, donde Piridina1 representa un compuesto del grupo de formulas (2) donde los asteriscos marcan el enlace con el cual el anillo de Piridina1 está unido a A; R1 representa alquilo C1-5, alcoxi C1-4, cicloalquilo C3-6, hidroximetilo, o NR1aR1b; R1a representa alquilo C1-4, R1b representa hidrogeno, o alquilo C1-3, o R1a y R1b, junto con el nitrogeno que está unido a la piridina, forman un anillo de pirrolidina; R2 representa hidrogeno, o alquilo C1-4, o en el caso en que R1 represente alquilo C1-5 o cicIoalquilo C3-6, R2 puede representar además rnetoxi; R3 representa alquilo C1-5, alcoxi C1-4, cicloalquilo C3-6, o NR3aR3b; R3a representa alquilo C1-4; R3b representa H, o alquilo C1-3; R4 representa alquilo C1-4, o H; R5 representa alquilo C1-5, metoxi, o NR5aR5b; y R6 representa alquilo C1-2; R5a representa alquilo C1-4; R5b representa H, o alquilo C1-3; o R5 representa alquilo C1-2, o metoxi; y R6 representa alquilo C1-5, o NR6aR6b; R6a representa alquilo C1-4; R6b representa hidrogeno, o alquilo C1-3; R7 representa alquilo C1-5; R8 representa alquilo C1-2, o metoxi; R9 representa alquilo C1-5; R10 representa alquilo C1-2; A representa un compuesto del grupo de las formulas (3), donde los asteriscos indican el enlace que está unido al anillo de Piridina1; Piridina2 representa un compuesto del grupo de formulas (4), donde los asteriscos marcan el enlace con el cual el anillo de Piridina2 está unido a A; R11 representa alquilo C1-4, alcoxi C1-3, hidroximetilo, o NR11aR11b; R11a representa alquilo C1-3, R11b representa hidrogeno, o alquilo C1-2, R12 representa hidrogeno, o alquilo C1-2, R13 representa alquilo C1-4, o representa NR13aR13b; R13a representa alquilo C1-3; R13b representa hidrogeno, o alquilo C1-2, R14 representa alquilo C1-2; R15 representa alquilo C1-4, o NR15aR15b; y R16 representa alquilo C1-2; R15a representa alquilo C1-3, R15b representa hidrogeno, o alquilo C1-3; o R15 representa alquilo C1-2; y R16 representa alquilo C1-4, o NR16aR16b; R16a representa alquilo C1-3; R16b representa hidrogeno, o alquilo C1-2; R17 representa alquilo C1-4; R18 representa alquilo C1-2, o metoxi; R19 representa alquilo C1-4; y R20 representa alquilo C1-2; con la excepcion de 3-(2-etil-4-piridil)-5-(2-etil-4-piridil)-1,2,4-oxadiazol; o una sal de dicho compuesto.Such compounds act particularly as immunomodulating agents. Claim 1: A compound of formula (1), Pyridine1-A-Pyridyria2, wherein Pyridine1 represents a compound of the group of formulas (2) wherein the asterisks mark the bond with which the ring of Pyridine1 is attached to A; R1 represents C1-5 alkyl, C1-4 alkoxy, C3-6 cycloalkyl, hydroxymethyl, or NR1aR1b; R1a represents C1-4 alkyl, R1b represents hydrogen, or C1-3 alkyl, or R1a and R1b, together with the nitrogen that is attached to pyridine, form a pyrrolidine ring; R2 represents hydrogen, or C1-4 alkyl, or in the case where R1 represents C1-5 alkyl or C3-6 cycloalkyl, R2 may further represent rnethoxy; R3 represents C1-5 alkyl, C1-4 alkoxy, C3-6 cycloalkyl, or NR3aR3b; R3a represents C1-4 alkyl; R3b represents H, or C1-3 alkyl; R4 represents C1-4 alkyl, or H; R5 represents C1-5 alkyl, methoxy, or NR5aR5b; and R6 represents C1-2 alkyl; R5a represents C1-4 alkyl; R5b represents H, or C1-3 alkyl; or R5 represents C1-2 alkyl, or methoxy; and R6 represents C1-5 alkyl, or NR6aR6b; R6a represents C1-4 alkyl; R6b represents hydrogen, or C1-3 alkyl; R7 represents C1-5 alkyl; R8 represents C1-2 alkyl, or methoxy; R9 represents C1-5 alkyl; R10 represents C1-2 alkyl; A represents a compound of the group of formulas (3), where the asterisks indicate the bond that is attached to the pyridine ring1; Pyridine2 represents a compound of the group of formulas (4), where the asterisks mark the link with which the Pyridine2 ring is attached to A; R11 represents C1-4 alkyl, C1-3 alkoxy, hydroxymethyl, or NR11aR11b; R11a represents C1-3 alkyl, R11b represents hydrogen, or C1-2 alkyl, R12 represents hydrogen, or C1-2 alkyl, R13 represents C1-4 alkyl, or represents NR13aR13b; R13a represents C1-3 alkyl; R13b represents hydrogen, or C1-2 alkyl, R14 represents C1-2 alkyl; R15 represents C1-4 alkyl, or NR15aR15b; and R16 represents C1-2 alkyl; R15a represents C1-3 alkyl, R15b represents hydrogen, or C1-3 alkyl; or R15 represents C1-2 alkyl; and R16 represents C1-4 alkyl, or NR16aR16b; R16a represents C1-3 alkyl; R16b represents hydrogen, or C1-2 alkyl; R17 represents C1-4 alkyl; R18 represents C1-2 alkyl, or methoxy; R19 represents C1-4 alkyl; and R20 represents C1-2 alkyl; with the exception of 3- (2-ethyl-4-pyridyl) -5- (2-ethyl-4-pyridyl) -1,2,4-oxadiazole; or a salt of said compound.

ARP080103611A 2007-08-17 2008-08-19 DERIVATIVES OF PIRIDINE AND ITS USE AS IMMUNOMODULATORS AR067977A1 (en)

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US (1) US8598208B2 (en)
EP (1) EP2195311B1 (en)
JP (1) JP5451614B2 (en)
KR (1) KR101541558B1 (en)
CN (1) CN102648198B (en)
AR (1) AR067977A1 (en)
AT (1) ATE502938T1 (en)
AU (1) AU2008290233B2 (en)
BR (1) BRPI0815190A2 (en)
CA (1) CA2695509A1 (en)
CY (1) CY1111830T1 (en)
DE (1) DE602008005770D1 (en)
DK (1) DK2195311T3 (en)
ES (1) ES2361463T3 (en)
HK (1) HK1144809A1 (en)
HR (1) HRP20110449T1 (en)
MA (1) MA31703B1 (en)
MX (1) MX2010001881A (en)
MY (1) MY153975A (en)
NZ (1) NZ583957A (en)
PL (1) PL2195311T3 (en)
PT (1) PT2195311E (en)
RU (1) RU2492168C2 (en)
SI (1) SI2195311T1 (en)
TW (1) TWI422373B (en)
WO (1) WO2009024905A1 (en)
ZA (1) ZA201001873B (en)

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